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Human Metabolome Database Version 3.5

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Showing metabocard for Gibberellin A3 (HMDB03559)

Record Information
Version 3.5
Creation Date 2006-08-12 17:44:01 -0600
Update Date 2013-05-21 14:32:26 -0600
HMDB ID HMDB03559
Secondary Accession Numbers None
Metabolite Identification
Common Name Gibberellin A3
Description Gibberellic acid, also called Gibberellin A3, GA, or GA3, is a very potent hormone whose natural occurrence in plants controls their development. Since GA regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect. Gibberellic acid is a hormone found in plants. Gibberelic acid is a simple gibberellin promoting growth and elongation of cells. Affects decomposition of plants. Helps plants grow if used in small amounts, but eventually plants grow a tolerance for it. Gibberellic acid stimulates the cells of germinating seeds to produce mRNA molecules that code for hydrolytic enzymes.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2b-Hydroxygibberellin 1
  2. Berelex
  3. Brellin
  4. GA3
  5. Gib-Sol
  6. Gib-Tabs
  7. Gibb-tabs
  8. Gibberelate
  9. Gibberelic acid
  10. Gibberelin
  11. Gibberellate
  12. Gibberellic acid
  13. Gibberellin
  14. Gibberellin 1
  15. Gibberellin X
  16. Gibberellins
  17. Gibberellinsaeure
  18. Gibberillate
  19. Gibberillic acid
Chemical Formula C19H22O6
Average Molecular Weight 346.3744
Monoisotopic Molecular Weight 346.141638436
IUPAC Name (1R,2R,5S,8S,9S,10R,11R,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1^{5,8}.0^{1,10}.0^{2,8}]heptadec-13-ene-9-carboxylic acid
Traditional IUPAC Name gibberellic acid
CAS Registry Number 77-06-5
SMILES [H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@]3(C)[C@@H](O)C=C[C@@]21OC3=O
InChI Identifier InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16+,17+,18+,19-/m1/s1
InChI Key IXORZMNAPKEEDV-SNTJWBGVSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Terpene Lactones
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Gamma Butyrolactone
  • Lactone
  • Oxolane
  • Secondary Alcohol
  • Sesquiterpene Backbone
  • Tertiary Alcohol
Direct Parent Gibberelins
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 234 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 5 mg/mL Not Available
LogP 0.24 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 1.95 g/L ALOGPS
LogP 0.66 ALOGPS
LogP 0.35 ChemAxon
LogS -2.25 ALOGPS
pKa (strongest acidic) 4.16 ChemAxon
pKa (strongest basic) -0.9 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 104.06 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 86.42 ChemAxon
Polarizability 48.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB013644
KNApSAcK ID C00000003 Link_out
Chemspider ID 7995349 Link_out
KEGG Compound ID C01699 Link_out
BioCyc ID CPD-6224 Link_out
BiGG ID Not Available
Wikipedia Link GA Link_out
NuGOwiki Link HMDB03559 Link_out
Metagene Link HMDB03559 Link_out
METLIN ID 6954 Link_out
PubChem Compound 9819600 Link_out
PDB ID Not Available
ChEBI ID 682248 Link_out
References
Synthesis Reference Lischewski, Manfred; Adam, Guenter. Gibberellin compounds. Ger. (East) (1979), 10 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Yamaki T, Takeda K: [A simple bioassay method of urinary indoleacetic acid, a cancer growth factor] J UOEH. 1986 Mar 20;8 Suppl:297-302. Pubmed: 3460143 Link_out